Bromine → HCID 13059708, compound

HRID 358457Notes

Reaction equation

HRID 358457 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:12])[CH2:7][CH2:8][S:9]2)=[CH:4][CH:3]=1.[Br:13]Br>C(Cl)(Cl)Cl>[Br:13][CH:7]1[C:6](=[O:12])[C:5]2[C:10](=[CH:11][C:2]([Cl:1])=[CH:3][CH:4]=2)[S:9][CH2:8]1

Participants

4

Reactant 2

HCID 24408BromineHCID 12283928HCID 12283928, compound

Product 1

HCID 13059708HCID 13059708, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Dissolve 7-chlorothiochroman-4-one (10 gms., 50.3 mmols) in chloroform (100 ml.) and cool the solution to 0°-5° C. Add bromine (2.60 ml., 50.3 mmols) dropwise over a 10-minute period. Stire the reaction mixture at room temperature for one hour, then add chloroform (100 ml.) and extract with 10% aqueous sodium sulfite (100 ml.) followed by water (200 ml.). Dry the chloroform solution over anhydrous magnesium sulfate, filter and evaporate in vacuo to a residue. Recrystallize the residue from cyclohexane to give 3-bromo-7-chlorothiochroman-4-one, m.p. 109°-110° C.

Workup

  1. temperaturecool the solution to 0°-5° C
  2. customat room temperature
  3. customfor one hour
  4. extractionadd chloroform (100 ml.) and extract with 10% aqueous sodium sulfite (100 ml.)
  5. dry with materialDry the chloroform solution over anhydrous magnesium sulfate
  6. filtrationfilter
  7. customevaporate in vacuo to a residue
  8. customRecrystallize the residue from cyclohexane

Sources & evidence

ORD record
ord-45622c1ac8b14226b82ec365a14ecb00
Source dataset
uspto-grants-1984_08
Patent number
US04468404

Reaction notes

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